Iron-Catalyzed α-Alkylation of Ketones with Alcohols

被引:249
作者
Elangovan, Saravanakumar [1 ,2 ]
Sortais, Jean-Baptiste [1 ]
Beller, Matthias [2 ]
Darcel, Christophe [1 ]
机构
[1] Univ Rennes 1, UMR CNRS 6226, Inst Sci Chim Rennes, Ctr Catalysis & Green Chem,Team Organometall Mat, F-35042 Rennes, France
[2] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
关键词
alkylation; borrowing hydrogen; homogeneous catalysis; Friedlander reaction; iron catalysts; CHIRAL BRONSTED ACID; COOPERATIVE TRANSITION-METAL; OPPENAUER-TYPE OXIDATION; BASE-MEDIATED SYNTHESIS; BORROWING HYDROGEN; ENANTIOSELECTIVE HYDROGENATION; REDUCTIVE AMINATION; COMPLEXES SYNTHESIS; SECONDARY ALCOHOLS; BOND FORMATION;
D O I
10.1002/anie.201506698
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A general and benign iron-catalyzed alpha-alkylation reaction of ketones with primary alcohols has been developed. The key to success of the reaction is the use of a Knolker-type complex as catalyst (2 mol%) in the presence of Cs2CO3 as base (10 mol%) under hydrogen-borrowing conditions. Using 2-aminobenzyl alcohol as alkylation reagent allows for the "green" synthesis of quinoline derivatives.
引用
收藏
页码:14483 / 14486
页数:4
相关论文
共 103 条
  • [1] Alcohols for the α-Alkylation of Methyl Ketones and Indirect Aza-Wittig Reaction Promoted by Nickel Nanoparticles
    Alonso, Francisco
    Riente, Paola
    Yus, Miguel
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (29) : 4908 - 4914
  • [2] [Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1002/ANGE.201201360
  • [3] [Anonymous], 2008, EUR J ORG CHEM
  • [4] The Catalytic Amination of Alcohols
    Baehn, Sebastian
    Imm, Sebastian
    Neubert, Lorenz
    Zhang, Min
    Neumann, Helfried
    Beller, Matthias
    [J]. CHEMCATCHEM, 2011, 3 (12) : 1853 - 1864
  • [5] Recent Advances in Iron Catalysis in Organic Synthesis
    Bauer, Eike B.
    [J]. CURRENT ORGANIC CHEMISTRY, 2008, 12 (16) : 1341 - 1369
  • [6] Iron Catalysis in Organic Synthesis
    Bauer, Ingmar
    Knoelker, Hans-Joachim
    [J]. CHEMICAL REVIEWS, 2015, 115 (09) : 3170 - 3387
  • [7] Light-Induced Enantioselective Hydrogenation Using Chiral Derivatives of Casey's Iron-Cyclopentadienone Catalyst
    Berkessel, Albrecht
    Reichau, Sebastian
    von der Hoeh, Adrian
    Leconte, Nicolas
    Neudoerfl, Joerg-M.
    [J]. ORGANOMETALLICS, 2011, 30 (14) : 3880 - 3887
  • [8] N-Heterocyclic Carbene Ligands and Iron: An Effective Association for Catalysis
    Bezier, David
    Sortais, Jean-Baptiste
    Darcel, Christophe
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (01) : 19 - 33
  • [9] Iridium catalysed chemoselective alkylation of 2′-aminoacetophenone with primary benzyl type alcohols under microwave conditions
    Bhat, Shailen
    Sridharan, Visuvanathar
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (39) : 4701 - 4703
  • [10] Borrowing hydrogen: iridium-catalysed reactions for the formation of C-C bonds from alcohols
    Black, PJ
    Cami-Kobeci, G
    Edwards, MG
    Slatford, PA
    Whittlesey, MK
    Williams, JMJ
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (01) : 116 - 125